Organizational clients

Your team needs to adopt AI—not just talk about it.

In a fast-changing economy, organizations can’t afford to stay on the sidelines. My training & coaching sessions are designed to close the gap between knowing AI matters and actually using it to get real work done.

These sessions are practical, fast-paced, and designed to help professionals use AI to think better, write faster, and move through projects with less friction. Just as importantly, your team will build shared language and norms—so using AI becomes a natural, integrated part of your team’s work.

Training sessions

Field-tested yet flexible: the content, emphasis, and examples can be tailored to match your organization’s goals, whether you're just getting started or deepening your AI fluency.

  • AI isn’t a magic typewriter, but it can be a powerful ally throughout the writing process. We’ll walk through how I collaborated with AI to write a LinkedIn post that got 400,000+ views and unpack the step-by-step approach behind that collaboration. From there, we’ll introduce a framework for working with AI at different stages of the writing process. We’ll close by highlighting common signs of weak LLM writing.

    Homework: Write or revise something using strategies from this session.

  • Projects can turn ChatGPT into a personal operating system—one that remembers your goals, holds relevant files, and supports your work. Learn to layer knowledge, project instructions, token memory, and prompting to create high-leverage workflows for tasks like writing, networking, and planning (whether your week or your meals).

    Homework: Create two Projects to assist your workflows—one for writing and one for something that matters to your work.

  • AI becomes far more powerful when it knows you. This session shows you how to build a lasting thought partnership using memory: one that evolves with your goals, adapts to your work style, and interacts with you in deeper ways. You’ll learn how to shape memory, define working “modes,” and use AI to surface habits, strengths, and growth edges.

    Homework: Teach AI something useful about your work and set up at least one “mode” that you want to be able to switch on at any time.

  • Learn how to use AI as an analytic partner. We’ll walk through how to collaborate with AI both inside spreadsheet environments and in broader analytic workflows—framing questions, guiding analysis, and extracting insights that go beyond the obvious. Whether you're working with surveys, financial data, or messy qualitative responses, you'll learn techniques to move from raw inputs to meaningful conclusions.

  • AI becomes far more powerful when it knows you. This session shows you how to build a lasting thought partnership using memory: one that evolves with your goals, adapts to your work style, and interacts with you in deeper ways. You’ll learn how to shape memory, define working “modes,” and use AI to surface habits, strengths, and growth edges.

    Homework: Teach AI something useful about your work and set up at least one “mode” that you want to be able to switch on at any time.

  • You’ll learn how to build Custom GPTs that capture expert judgment and deliver consistent, high-quality support across teams, use cases, or client needs. Whether you're automating document review, simulating conversations, or guiding others through complex workflows, GPTs let you hand off not just tasks but also your way of thinking. By the end, you’ll know when to use a Custom GPT, how to design one well, and how to turn AI into a scalable extension of your work.

What organizational engagements offer

  • Extended depth: 90 minutes, with space to learn concepts and move into live application with your team.

  • Tailored content: Adjusted for your organization’s adoption stage (beginner to advanced) and your priorities (adding/dropping topics as needed).

  • Shared baseline: Everyone learns the same language and practices together, accelerating culture change.

  • Designed for implementation: Built-in time for collaboration means progress starts during the sessio.

Your instructor

I’m Sarah Dillard, an entrepreneur and educator.

I first got interested in LLM tools after reading collected pieces about them in the 2020 Best American Science & Nature Writing. This led me to start experimenting before ChatGPT had even launched. When it did, it immediately felt like a game-changer. So much so that I wrote the first education sector op-ed on ChatGPT: “Schools Must Embrace the Looming Disruption of ChatGPT.”

You & AI has grown from a side project into a full-time job. I also advise Harvard Business School on the design of Foundry, their online entrepreneurship program, with a focus on how AI is reshaping what—and how—we teach.

I have an MBA from Harvard Business School & an MPP from the Harvard Kennedy School and started my career at Bain & Company. When not collaborating with AI, I enjoy hiking, hosting friends, and hanging out with my nieces (7 & 4).

Let’s work together

Curious what this could look like for your team?

Whether you're looking for a full training series to bring your team up to speed or a coaching engagement to work through a specific challenge, I’ll help you scope the right fit.

I’ve worked with teams across sectors—in education, philanthropy, tech, and investing—and am experienced in tailoring sessions to clients’ goals, tools, and existing fluency.

FAQs

  • One of the benefits of an organizational engagement is that I can tailor the training to meet your team where it is, whether they are just getting started or already regular users of AI tools.

  • I'll demo from a paid ChatGPT account ($20-$30/month), which has more powerful features than free accounts.

    ChatGPT’s core feature set is very similar to those of Claude & Gemini, and I have had many people (happily) complete the workshop series using these tools.

    I will also use NotebookLM as part of the Knowledge Partner session.